# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_mo_wj_ft_0m
_database_code_depnum_ccdc_archive 'CCDC 2160259'
loop_
_audit_author_name
_audit_author_address
'Jing Wang'
;Jilin Normal University 
China
;
_audit_update_record             
;
2022-03-20 deposited with the CCDC.	2022-07-28 downloaded from the CCDC.
;
_audit_creation_date             2019-01-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        1,10-Phenanthroline-1,2,4,5-tetracyanobenzene
_chemical_formula_moiety         'C12 H8 N2, C10 H2 N4'
_chemical_formula_sum            'C22 H10 N6'
_chemical_formula_weight         358.36
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   16.5206(5)
_cell_length_b                   7.6490(3)
_cell_length_c                   14.4843(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.5500(10)
_cell_angle_gamma                90
_cell_volume                     1829.65(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8061
_cell_measurement_temperature    297.15
_cell_measurement_theta_max      26.371
_cell_measurement_theta_min      2.935
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6301
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            26601
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.243
_diffrn_reflns_theta_max         26.417
_diffrn_reflns_theta_min         2.814
_diffrn_ambient_temperature      297.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71076
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2339
_reflns_number_total             3757
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.022(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3757
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0886
_refine_ls_R_factor_gt           0.0473
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0517P)²+0.5739P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1085
_refine_ls_wR_factor_ref         0.1426
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C13(H13), C14(H14), C17(H17), C18(H18), C19(H19), C20(H20),
 C21(H21), C22(H22)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.28827(10) 0.4846(2) 0.49870(12) 0.0684(5) Uani 1 1 d . . . . .
N2 N 0.14146(10) 0.3414(2) 0.44801(11) 0.0678(5) Uani 1 1 d . . . . .
C1 C 0.15290(11) 0.3991(2) 0.53626(12) 0.0519(4) Uani 1 1 d . . . . .
C2 C 0.39091(11) 0.3211(3) 0.18735(12) 0.0545(5) Uani 1 1 d . . . . .
C3 C 0.35047(11) 0.3079(3) 0.27121(12) 0.0565(5) Uani 1 1 d . . . . .
C4 C 0.22969(11) 0.4772(2) 0.56250(13) 0.0537(5) Uani 1 1 d . . . . .
C5 C 0.23390(11) 0.4443(3) 0.20160(13) 0.0554(5) Uani 1 1 d . . . . .
C6 C 0.27219(11) 0.3707(3) 0.27832(13) 0.0592(5) Uani 1 1 d . . . . .
H6 H 0.245708 0.363505 0.334040 0.071 Uiso 1 1 calc R . . . .
N3 N 0.08721(12) 0.5568(3) 0.21171(15) 0.0895(6) Uani 1 1 d . . . . .
C7 C 0.27376(12) 0.4569(3) 0.11791(12) 0.0564(5) Uani 1 1 d . . . . .
C8 C 0.35256(12) 0.3961(3) 0.11177(13) 0.0602(5) Uani 1 1 d . . . . .
H8 H 0.379495 0.406116 0.056467 0.072 Uiso 1 1 calc R . . . .
C9 C 0.09225(11) 0.3871(3) 0.60227(13) 0.0581(5) Uani 1 1 d . . . . .
C10 C 0.47166(13) 0.2517(3) 0.18156(13) 0.0670(6) Uani 1 1 d . . . . .
C11 C 0.24135(12) 0.5408(3) 0.65318(13) 0.0600(5) Uani 1 1 d . . . . .
C12 C 0.15201(13) 0.5067(3) 0.20762(14) 0.0656(6) Uani 1 1 d . . . . .
N4 N 0.53490(12) 0.1930(3) 0.17866(14) 0.0939(7) Uani 1 1 d . . . . .
C13 C 0.10636(14) 0.4548(3) 0.69246(14) 0.0717(6) Uani 1 1 d . . . . .
H13 H 0.065439 0.448887 0.735193 0.086 Uiso 1 1 calc R . . . .
C14 C 0.17750(15) 0.5270(3) 0.71718(14) 0.0720(6) Uani 1 1 d . . . . .
H14 H 0.185439 0.568885 0.777016 0.086 Uiso 1 1 calc R . . . .
N5 N 0.20193(14) 0.5930(3) -0.02536(15) 0.0994(7) Uani 1 1 d . . . . .
C15 C 0.23337(14) 0.5327(3) 0.03810(15) 0.0704(6) Uani 1 1 d . . . . .
N6 N 0.42709(13) 0.1571(4) 0.40593(15) 0.1057(8) Uani 1 1 d . . . . .
C16 C 0.39178(13) 0.2251(3) 0.34782(15) 0.0736(6) Uani 1 1 d . . . . .
C17 C 0.01871(13) 0.3069(3) 0.57534(17) 0.0732(6) Uani 1 1 d . . . . .
H17 H -0.022450 0.294667 0.617413 0.088 Uiso 1 1 calc R . . . .
C18 C 0.07054(14) 0.2695(3) 0.42681(17) 0.0788(7) Uani 1 1 d . . . . .
H18 H 0.061891 0.230771 0.366488 0.095 Uiso 1 1 calc R . . . .
C19 C 0.31637(14) 0.6166(3) 0.67628(17) 0.0756(6) Uani 1 1 d . . . . .
H19 H 0.326520 0.659411 0.735564 0.091 Uiso 1 1 calc R . . . .
C20 C 0.35769(14) 0.5594(3) 0.52443(18) 0.0822(7) Uani 1 1 d . . . . .
H20 H 0.398072 0.566900 0.481095 0.099 Uiso 1 1 calc R . . . .
C21 C 0.00828(14) 0.2478(3) 0.48776(19) 0.0807(7) Uani 1 1 d . . . . .
H21 H -0.039779 0.193616 0.468922 0.097 Uiso 1 1 calc R . . . .
C22 C 0.37399(15) 0.6273(3) 0.6119(2) 0.0843(7) Uani 1 1 d . . . . .
H22 H 0.423707 0.679207 0.625977 0.101 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C4 1.357(2) . ?
N1 C20 1.326(3) . ?
N2 C1 1.361(2) . ?
N2 C18 1.323(3) . ?
C1 C4 1.444(3) . ?
C1 C9 1.406(2) . ?
C2 C3 1.406(2) . ?
C2 C8 1.375(3) . ?
C2 C10 1.440(3) . ?
C3 C6 1.386(3) . ?
C3 C16 1.434(3) . ?
C4 C11 1.409(3) . ?
C5 C6 1.383(3) . ?
C5 C7 1.398(3) . ?
C5 C12 1.439(3) . ?
C6 H6 0.9300 . ?
N3 C12 1.140(3) . ?
C7 C8 1.387(3) . ?
C7 C15 1.441(3) . ?
C8 H8 0.9300 . ?
C9 C13 1.419(3) . ?
C9 C17 1.406(3) . ?
C10 N4 1.139(3) . ?
C11 C14 1.427(3) . ?
C11 C19 1.401(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.339(3) . ?
C14 H14 0.9300 . ?
N5 C15 1.141(3) . ?
N6 C16 1.137(3) . ?
C17 H17 0.9300 . ?
C17 C21 1.353(3) . ?
C18 H18 0.9300 . ?
C18 C21 1.383(3) . ?
C19 H19 0.9300 . ?
C19 C22 1.353(3) . ?
C20 H20 0.9300 . ?
C20 C22 1.389(3) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C20 N1 C4 117.00(19) . . ?
C18 N2 C1 116.90(18) . . ?
N2 C1 C4 118.69(16) . . ?
N2 C1 C9 122.28(18) . . ?
C9 C1 C4 119.02(17) . . ?
C3 C2 C10 119.12(18) . . ?
C8 C2 C3 119.88(17) . . ?
C8 C2 C10 120.98(17) . . ?
C2 C3 C16 118.22(17) . . ?
C6 C3 C2 120.37(18) . . ?
C6 C3 C16 121.40(17) . . ?
N1 C4 C1 118.41(17) . . ?
N1 C4 C11 122.56(18) . . ?
C11 C4 C1 119.03(17) . . ?
C6 C5 C7 120.57(17) . . ?
C6 C5 C12 119.75(17) . . ?
C7 C5 C12 119.67(18) . . ?
C3 C6 H6 120.4 . . ?
C5 C6 C3 119.25(17) . . ?
C5 C6 H6 120.4 . . ?
C5 C7 C15 120.30(18) . . ?
C8 C7 C5 119.80(18) . . ?
C8 C7 C15 119.90(17) . . ?
C2 C8 C7 120.11(17) . . ?
C2 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C1 C9 C13 119.98(19) . . ?
C17 C9 C1 117.77(19) . . ?
C17 C9 C13 122.25(19) . . ?
N4 C10 C2 178.0(3) . . ?
C4 C11 C14 119.69(19) . . ?
C19 C11 C4 117.61(19) . . ?
C19 C11 C14 122.7(2) . . ?
N3 C12 C5 179.4(3) . . ?
C9 C13 H13 119.4 . . ?
C14 C13 C9 121.21(19) . . ?
C14 C13 H13 119.4 . . ?
C11 C14 H14 119.5 . . ?
C13 C14 C11 121.1(2) . . ?
C13 C14 H14 119.5 . . ?
N5 C15 C7 179.5(3) . . ?
N6 C16 C3 177.0(2) . . ?
C9 C17 H17 120.2 . . ?
C21 C17 C9 119.5(2) . . ?
C21 C17 H17 120.2 . . ?
N2 C18 H18 117.6 . . ?
N2 C18 C21 124.8(2) . . ?
C21 C18 H18 117.6 . . ?
C11 C19 H19 120.2 . . ?
C22 C19 C11 119.7(2) . . ?
C22 C19 H19 120.2 . . ?
N1 C20 H20 117.9 . . ?
N1 C20 C22 124.2(2) . . ?
C22 C20 H20 117.9 . . ?
C17 C21 C18 118.7(2) . . ?
C17 C21 H21 120.7 . . ?
C18 C21 H21 120.7 . . ?
C19 C22 C20 118.9(2) . . ?
C19 C22 H22 120.5 . . ?
C20 C22 H22 120.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C4 C11 C14 -179.25(19) . . . . ?
N1 C4 C11 C19 1.1(3) . . . . ?
N1 C20 C22 C19 0.5(4) . . . . ?
N2 C1 C4 N1 -2.1(3) . . . . ?
N2 C1 C4 C11 178.60(18) . . . . ?
N2 C1 C9 C13 -177.80(19) . . . . ?
N2 C1 C9 C17 2.1(3) . . . . ?
N2 C18 C21 C17 1.6(4) . . . . ?
C1 N2 C18 C21 -0.7(4) . . . . ?
C1 C4 C11 C14 0.0(3) . . . . ?
C1 C4 C11 C19 -179.67(17) . . . . ?
C1 C9 C13 C14 -1.6(3) . . . . ?
C1 C9 C17 C21 -1.2(3) . . . . ?
C2 C3 C6 C5 0.9(3) . . . . ?
C3 C2 C8 C7 -0.8(3) . . . . ?
C4 N1 C20 C22 0.9(4) . . . . ?
C4 C1 C9 C13 1.4(3) . . . . ?
C4 C1 C9 C17 -178.64(18) . . . . ?
C4 C11 C14 C13 -0.1(3) . . . . ?
C4 C11 C19 C22 0.4(3) . . . . ?
C5 C7 C8 C2 1.1(3) . . . . ?
C6 C5 C7 C8 -0.4(3) . . . . ?
C6 C5 C7 C15 179.65(19) . . . . ?
C7 C5 C6 C3 -0.6(3) . . . . ?
C8 C2 C3 C6 -0.2(3) . . . . ?
C8 C2 C3 C16 178.5(2) . . . . ?
C9 C1 C4 N1 178.63(18) . . . . ?
C9 C1 C4 C11 -0.7(3) . . . . ?
C9 C13 C14 C11 0.9(3) . . . . ?
C9 C17 C21 C18 -0.5(4) . . . . ?
C10 C2 C3 C6 -178.85(19) . . . . ?
C10 C2 C3 C16 -0.1(3) . . . . ?
C10 C2 C8 C7 177.84(19) . . . . ?
C11 C19 C22 C20 -1.2(4) . . . . ?
C12 C5 C6 C3 178.71(19) . . . . ?
C12 C5 C7 C8 -179.69(18) . . . . ?
C12 C5 C7 C15 0.3(3) . . . . ?
C13 C9 C17 C21 178.8(2) . . . . ?
C14 C11 C19 C22 -179.2(2) . . . . ?
C15 C7 C8 C2 -178.97(19) . . . . ?
C16 C3 C6 C5 -177.8(2) . . . . ?
C17 C9 C13 C14 178.5(2) . . . . ?
C18 N2 C1 C4 179.54(19) . . . . ?
C18 N2 C1 C9 -1.2(3) . . . . ?
C19 C11 C14 C13 179.5(2) . . . . ?
C20 N1 C4 C1 179.03(19) . . . . ?
C20 N1 C4 C11 -1.7(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
